


Hawkwood Prison Blues

by adderair



Category: Supernatural
Genre: Abusive John Winchester, Alternate Universe - Prison, BAMF Dean Winchester, But hes dead, Childhood Memories, Dean Winchester is Sam Winchester's Parent, Flashbacks, John Winchester Being an Asshole, Killer Dean Winchester, Killer Sam Winchester, Kinda, Memories, Nerd Castiel (Supernatural), Nerd Sam Winchester, On the Run, Prison AU, Protective Dean Winchester, Protective Sam Winchester, Serial Killer Dean Winchester, Serial Killer Sam Winchester, prison break - Freeform, prison warden crowley, roadtrip?, shurleys are a crime family, so its ok
Language: English
Status: In-Progress
Published: 2020-06-20
Updated: 2020-06-20
Packaged: 2021-03-04 04:40:30
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 971
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24817750
Author URL: https://archiveofourown.org/users/adderair/pseuds/adderair
Summary: When Dean Winchester comes to Gabriel Shurley with a plan to escape prison, He's skeptical. Escaping the highest max prison on the eastern seaboard sounds hard enough with just Dean and his brother, but adding Gabriel and his brothers to the mix? Well, let it be said that Gabriel doesn't love a challenge, and he's always up for causing a bit of mischief.Alternatively; Supernatural prison AU where they decide to escape prison and go on the run together.
Relationships: Gabriel/Dean Winchester
Comments: 3
Kudos: 18





	Hawkwood Prison Blues

Gabriel Shurley leaned against the fence and idly twirled a lollipop around in his mouth. The sun beams directly overhead, and if he squints through the sturdy metal fencing, he can see the heat rising from the unending pavement. It wouldve been nice out, he thinks, if there'd been a breeze. The sky is a pale blue and dotted sparesely with clouds, and the birds are chirping. However, the air is stagnant, thick, hot, and oppressive, hanging over the prison yard like a heavy winter blanket. behind him the other inmates who decided to endure the heatwave are lifting weights, talking, and some brave (stupid) souls are heckling the guards. with a sigh, he turns around and ambles his way over to his brothers.  
  
The Shurley crime family was like something out of a comic book ot T.V. show. Powerful, elusive, and expansive. They mostly meddled in drugs, but had gotten a taste for smuggling weaponry a few months before they all got caught.  
  
Frankly, it'd been embarrassing. The feds had come down on them in one fell swoop and charted all the Shurley boys off to prison. That'd been a year ago, and since then they'd made a name for themselves once again, this time inside the bars. Smuggling food, drinks, and other assorted contraband inside the 'Highest Security Prison on the West Coast' was suprisingly easy. Also kinda sad.  
  
"Sam and Dean have been asking for whiskey and some "Busty Asian Beauties" lately." Lucifer was saying, with a roll of his eyes, as Gabriel approached. Castiel let out a quiet laugh,  
  
"You mean Dean's been asking." He corrects with a twinkle of mirth in his blue eyes.  
  
"Course he does." Gabriel laughs, slotting his way into the conversation easily, "Dean's the only one who asks for shit like that."  
  
Dean and Sam Winchester, the only people in this prison who even stood anywhere near The Shurleys. Their mother had died when they were little, and their Dad had gone on a murder spree, dragging his sons across the country, and having them assist him in his kills. That fuckwad what thankfully died about 6 years back, after he'd split from his sons. Apparently he'd been caught redhanded, and after a brief shootout, had gotten a bullet to the brains for his troubles.  
  
His sons though, yikes. Gabriel had learned, solely from rumors and gossip, that the Winchesters had followed in their Daddy's footsteps and gone on to a three year cross country killing spree. They'd been brought in a few times, but had always managed to escape before they could be charted off to jail. Usually, their escapes encluded a station full of dead police officers, and once, a exploed helicopter. In Hawkwood correctional facility, they were pretty chill, keeping to themselves and almost painfully codependant. When they'd first been admitted they'd been put in seperate cells, but after a week of nonstop riots, and many injuries, had been allowed to share a cell.  
  
Despite their fearsome reputation and frankly terrifying apperances, They were actually pretty good company, at least in Gabriel's opinion. He was pretty sure Cassie agreed with him too. Dean could spend hours talking about his 'Baby', a 1967 Chevrolet Impala, and shared Gabriel's affinity for sweets, though he preffered pie. He could tell you 63 ways to gut a man, how to fix a broken taillight, and how to make the best damn cocktail Gabriel had ever tasted. He enraptured himself with 'Busty Asian Beauties', could tell you how to take pretty much any gun apart, and could boast about his brother in such a way you forgot that they were both terrifying killers with over 100 kills under their belts.  
  
Sam on the other hand was more reserved, kept to himself more, and could often be found, book in hand, sitting just within Dean's eyesight. For a 6'4" man, he had amazing puppy dog eyes, and somehow never seemed to be a looming, imposing presence. Despite being a murderer, he really couldn't be described as anything but a massive ball of sunshine and floppy hair. Not to say he wasnt just as terryfing as his brother, but he seemed to be the yin to Dean's yang. He and Castiel got along quite well, as they were both bookish and a bit nerdy.  
  
Michael constantly complained about the Winchesters, but all of his brothers ignored him. even Luci, who was a bit of a prick. They were maybe Gabriel's only real friends in this hellhole, sue him.  
  
"Heard you talkin' about me." Came a sudden voice from behind Gabriel's shoulder, and he jumped, turning around with a squawk. He could have sworn Dean wasnt their a few seconds ago. A light chuckle gave away Sam's presence as well. How they could sneak around like that in garish orange jumpsuits, Gabe would never know. As he meet Dean's mossy green eyes, crinkled with amusement, he relaxed marginally.  
  
"What the hell man? sneaking up behind me like that? Could'a killed me! I could've choked on my lollipop and died, and it would'a been all you fault." He cried, outraged, lightly slugging Dean in the shoulder. Dean moved with the direction of the punch, softening the blow, before he turned his attention to Michael, who watched with a slightly constipated look.  
  
"Whatcha think, mikey?" He asked, "Care to dig that stick outta your ass and give your dear sweet friend a nice ol' copy of 'Busty Asian Beauties'?" Michael sighed wearly.  
  
"Fine." He said, "I'll talk to Raymond about it. You owe us though." then, with a put upon glance at Lucifer, he turned and headed towards their favorite guard, Raymond, a portly pig of a man, who was just barely competent enough to help them smuggle in contraband.  
  
Dean watched him go with a cheery grin.


End file.
